Buying Online Businesses Podcast

Exiting a business can be one of the most rewarding moments of an entrepreneur’s journey—or one of the most costly mistakes if handled poorly. Many sellers unknowingly leave hundreds of thousands, even millions of dollars, on the table simply because they aren’t prepared for the exit process. Jaryd Krause speaks with Domenic Rinaldi, a seasoned M&A advisor and owner of Sun Acquisitions, who has successfully guided over 500 business transactions. As the founder of K2 Advisor, Domenic specializes in helping business owners understand exactly what it takes to execute a profitable and stress-free exit. Together, they break down the biggest mistakes sellers make when exiting their businesses and how to avoid them.  You’ll discover: ✔️ How owner involvement and single-source dependencies can destroy your business valuation ✔️ Why many sellers are blindsided by market shifts, tariffs, and environmental changes ✔️ The critical role of value drivers and how to identify them before going to market ✔️ What can go catastrophically wrong during a deal—and how the right advisory team can prevent it ✔️ Why you should always be “exit ready,” even if selling isn’t on your immediate horizon If you’re preparing to sell your business—or simply want to protect the value you’ve built—this episode is packed with actionable insights to help you exit on top. 🎧 Listen now and learn how to exit your business the smart way. Episode Highlights 02:18 – Why most sellers leave money on the table when exiting their business 05:42 – How owner dependence and single-source revenue can destroy valuation 08:15 – Common risks in the current market, including tariffs and environmental changes 11:35 – Value drivers Domenic looks for when assessing a business for sale 14:50 – The importance of due diligence and how small oversights can become costly 17:30 – Why sellers must always be “exit-ready,” even if they’re not planning to sell soon 20:10 – Choosing the right advisory team: lawyers, accountants, and M&A experts who can make or break your exit Key Takeaways ➥ Seller mistakes are costly. Failing to prepare for an exit can result in leaving hundreds of thousands—or even millions—of dollars on the table. ➥ Owner dependency kills value. Businesses overly reliant on the owner, single customers, or single traffic sources are heavily discounted by buyers. ➥ Market conditions matter. External factors like tariffs, environmental shifts, or regulatory changes can impact valuation. Smart sellers plan for these contingencies in advance. ➥ Value drivers determine your sale price. Revenue diversity, strong cash flow, and documented systems all increase buyer confidence and the multiple you can command. ➥ Due diligence is non-negotiable. Small errors or overlooked liabilities can derail a deal. A proactive approach prevents last-minute surprises. ➥ Always be exit-ready. Even if you’re not planning to sell, setting up your business for a smooth exit ensures you’re prepared for unexpected life events or market opportunities. ➥ The right team is critical. Experienced lawyers, accountants, and M&A advisors can prevent deal disasters and protect your financial outcome.   About Domenic Rinaldi A seasoned M&A adviser, Domenic Rinaldi is the Owner and Managing Partner of the firm, Sun Acquisitions. He also founded K2Adviser to educate business owners on the requirements for a successful exit, acquisition, or scaling process.     Connect with Domenic Rinaldi ➥https://buyingonlinebusinesses.com/ep-087-why-you-need-seasoned-vets-on-your-team-when-buying-selling-businesses/ ➥www.sunacquisitions.com   Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/ ➥ GoDaddy (Website Hosting) - https://bit.ly/3YiRkWV ➥ Non Agency (SEO Audit) - https://bit.ly/3EPd7OZ ➥ Market Muse (Content Marketing Software) - https://bit.ly/3Me39L0   🔥Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO➥ Investors Club - https://bit.ly/3ZpgioR   *This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.See omnystudio.com/listener for privacy information.

Running a business is about building something that works without you, not just putting in the hours. But far too many entrepreneurs stay stuck in the weeds, overwhelmed by daily tasks and unclear on how to truly scale. That’s where systems—and now, AI—change everything. In this conversation, Jaryd Krause is joined by David Jenyns, founder of Systemology and author of SYSTEMology and The Systems Champion, to unpack how smart systems combined with the power of AI are transforming the way online businesses grow. David has built and sold multiple companies, helped hundreds of business owners systemize their operations, and now leads the conversation on how AI can be used not just to support teams, but to replace certain roles altogether. You’ll learn: ✔️ How to use AI to build and improve systems in your business✔️ Why experienced talent plus AI is replacing the traditional VA model✔️ How to step back from your business without losing momentum✔️ Real-life examples of AI replacing inefficiencies and boosting profits When it comes to growing your business, reclaiming your time, and creating something that endures, this episode is packed with useful strategies and steps to follow. 🎧 Tune in now and learn how to scale smarter with the systems + AI advantage.   Episode Highlights 01:44 – Why systemizing your business is critical for growth and freedom 06:15 – How to commit fully and overcome resistance when building systems 12:30 – The role and impact of a systems champion in scaling your business 19:30 – Where a systems champion fits in and how to identify the right person 22:00 – The transformative power of AI in systemizing processes and operations 27:30 – Real-life example of AI disrupting traditional business documentation 32:00 – How AI enhances the productivity of skilled team members and shrinks teams 35:00 – Using AI strategically to outperform competitors and grow faster   Key Takeaways ➥ Committing fully to systemizing your business culture is essential; half-measures lead to failure due to team resistance. ➥ Hiring a systems champion is critical—they drive the systemization process and embed a culture of repeatability and efficiency. ➥ Business owners need to shift focus from daily tasks to strategic growth, enabled by well-documented systems and strong teams. ➥ AI tools like ChatGPT and Google Gemini accelerate system documentation, process optimization, and strategic decision-making. ➥ AI adoption leads to smaller, more skilled teams who leverage technology to produce higher-quality results. ➥ Privacy concerns around AI data use require careful selection of secure platforms to protect business information. ➥ The systems champion role is evolving to include AI management, programming workflows, and ensuring the accuracy of AI outputs. ➥ Businesses embracing AI and systems now will stay competitive; those who resist risk falling behind in a rapidly changing landscape.   About David Jenyns David Jenyns is an experienced entrepreneur who sold the Melbourne Cricket Ground in his early twenties and founded Melbourne SEO Services. He systematized himself out of that business in 2016 and founded SYSTEMology to help business owners implement systems to scale their business. Today, he supports a growing community of certified SYSTEMologists, delivers workshops, keynote addresses hosts a podcast, and is on a mission to free business owners worldwide from daily operations.    Connect with David Jenyns ➥ https://www.systemology.com/scbook/ ➥ https://www.systemology.com/   Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/ ➥ Site Ground (Website Hosting) - https://bit.ly/3JBEC1u ➥ Rank Math (Wordpress SEO Plugin) - https://bit.ly/3Acyjf4 ➥ Convert Kit  (Email Service Provider) - https://bit.ly/3o10Xgx   🔥Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO➥ Investors Club - https://bit.ly/3ZpgioR   *This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.See omnystudio.com/listener for privacy information.

Understanding the fine print that could make or break your deal is just as important when purchasing a business with SBA financing as it is when obtaining a loan. All too frequently, buyers lose out on opportunities or become mired in transactions that don't fit the program because they are unaware of the nuances of SBA regulations. The CEO of SBA Loan Group, Yankie Markowitz, sits down with Jaryd Krause in this episode to discuss his extensive knowledge of SBA loans and how he has facilitated more than $1 billion in SBA and real estate transactions. Yankie explains which business categories are eligible for SBA financing, what has changed recently, and how to handle the complex world of debt ratios, deal structures, and cash requirements. You’ll learn: ✔️ Which businesses can—and can’t—be acquired with SBA loans ✔️ How much cash do you need to qualify ✔️ Why e-commerce fits well with SBA financing, and where it falls short ✔️ The ins and outs of seller notes, holdbacks, and loan terms ✔️ Real-world lessons from deals that worked—and ones that didn’t This episode provides useful, straightforward advice from one of the most seasoned SBA specialists in the industry, regardless of whether you're prepared to purchase your first company or want to improve your acquisition approach. 🎧 To learn how to make SBA financing work for you and get closer to financial independence, listen now.   Episode Highlights 06:15 – Eligibility requirements and the role of creditworthiness in SBA loan approval 10:30 – Structuring deposits and how larger down payments can secure better interest rates 15:45 – Differences in loan terms and amortization for business vs. real estate purchases 20:20 – Prepayment penalties and their impact on SBA loan flexibility 23:00 – Utilizing seller notes and financing strategies in SBA deals 29:50 – Debt service coverage ratios and the importance of consistent cash flow Key Takeaways ➥ SBA financing is highly versatile, supporting working capital, inventory, real estate, and refinancing, but buyers must understand eligibility and lender-specific nuances. ➥ Seller financing (seller notes) can be incorporated into SBA deals but requires careful structuring to meet lender requirements and ensure adequate cash flow. ➥ Business valuation multiples generally range from 3-5x EBITDA for traditional businesses; higher multiples (like software businesses) often require substantially more equity upfront. ➥ Owning an existing profitable business simplifies acquiring complementary businesses by leveraging combined cash flow to support additional debt. ➥ Sustainable growth beats rapid expansion; business owners must carefully manage operational costs and cash flow to avoid overextension post-acquisition.   About Yankie Markowitz Yankie Markowitz is the Chief Executive Officer of SBA Loan Group. Yankie has helped facilitate over $1 billion dollars in SBA and real estate transactions, and complex deal syndication. He is often sought out by bankers to help structure intricate SBA transactions because of his knowledge and unique experience with the U.S. Small Business Administration loan programs.  Yankie is an Executive Board member for the Regional Business Assistance Corporation (an SBA CDC) and has been on the Loan Committee which allows him to work on hundreds of transactions for SBA each year. He also serves as a Board Member of Crown Heights Young Entrepreneur, a non-profit that is a full-service business resource center specifically tailored to fit the unique needs for aspiring entrepreneurs that focus on promoting responsible business development and providing them with the tools and resources that they need in order to achieve lifelong financial independence.    Connect with Yankie Markowitz ➥ https://sbaloangroup.com/ ➥https://finwise.podbean.com/e/finwise-eye-on-sba-lending-yankie-markowitz-ceo-sba-loan-group/   Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/ ➥ Hostinger (Website Hosting) - https://bit.ly/3HUqW0s ➥ Rank Math (Wordpress SEO Plugin) - https://bit.ly/3Acyjf4 ➥ Ezoic (Ad Network) - https://bit.ly/3NuVR5P 🔥Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO ➥ Investors Club - https://bit.ly/3ZpgioR   *This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.See omnystudio.com/listener for privacy information.

Buying or selling a business isn’t just a transaction — it’s a turning point. But too often, what buyers think they want and what sellers believe they deserve don’t line up with reality. The result? Stalled deals, missed opportunities, and plenty of frustration on both sides. In this episode, Jaryd Krause sits down with Matt Frisca, owner of Transworld Business Advisors of La Grange and Tinley Park, to unpack the biggest reasons deals fail—and what it really takes to make them work. With 20+ business sales closed annually and 50+ active listings, Matt shares real-world insights from both sides of the table. You’ll learn: ✔️ Why sellers struggle to exit cleanly✔️ Common mistakes buyers make (and how to avoid them)✔️ The truth about SBA financing and “no money down” deals✔️ What due diligence really looks like in today’s market Whether you're buying, selling, or just curious, this episode delivers raw advice and actionable strategies from a dealmaker who knows the game. 🎧 Listen now and get the inside track on what actually moves the needle in business acquisitions.   Episode Highlights 12:40 – Importance of motivated sellers and avoiding lead oversaturation 15:45 – The three biggest reasons businesses fail to sell: lack of motivation, messy financials, and unrealistic pricing 19:30 – Recent SBA lending rule changes and fees 22:45 – Why “no money down” deals are unrealistic 24:40 – Risks of inexperienced buyers buying big businesses 28:10 – How to be an attractive, prepared buyer 33:15 – Balancing due diligence and trust to avoid “paralysis by analysis”   Key Takeaways ➥ Motivated sellers, clean financials, and realistic prices are crucial.➥ Content marketing is replacing paid ads due to cost hikes.➥ Seller equity rollovers now carry higher risk for sellers.➥ “No money down” deals rarely work; buyers need funds and experience.➥ Private equity adds competition for deals under $5M.➥ Prepared buyers with financing and clear plans succeed more.➥ Avoid overanalyzing—take calculated risks to close deals.   About Matt Frisca Matt Friscia runs and owns the Transworld Business Advisors of La Grange and Tinley Park with his team of 9 agents and one administrative assistant, focusing on main street and lower mid-market business brokerage. Their office handles over 20 successful closes a year, and they typically are working 50+ business for sale listings at any given time. Before joining Transworld, Matt worked in media sales for 15 years. Ten of those years were with the Disney company within their ESPN, ABC, and Radio Disney brands. He bought his first business, which was a franchise in the senior care field, back in 2016. He successfully grew that company and ultimately sold it five years later with Transworld Business Advisors.  His passion is helping small business owners with their business exit transactions while helping to super serve the underserved community of small businesses. Besides having played music professionally for the past 28 years, he enjoys watching his two children play sports, traveling and learning languages.   Connect with Matt Frisca ➥ https://www.tworld.com/    Resource Links ➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/ ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause ➥ Cloud Ways (Website Hosting) - https://bit.ly/40tjyjG ➥ Link Whisper (SEO tool for internal linking on websites) - https://bit.ly/3l7K7Ld ➥ Convert Kit (Email Software Provider) - https://bit.ly/3o10Xgx   🔥Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO ➥ Investors Club - https://bit.ly/3ZpgioR   *This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.See omnystudio.com/listener for privacy information.

Let’s be real — buying or selling a business is one of the biggest decisions you’ll ever make. Get it right, and it could be life-changing. Get it wrong… and the fallout could be brutal. That’s exactly why this week’s episode is a must-listen. Jaryd Krause sits down with Katarina Strandberg, a powerhouse Swedish business lawyer with deep expertise in venture capital, scale-ups, and M&A. She’s worked with founders, investors, and SME leaders across Europe, and brings not only legal chops but also perspective as an angel investor, published author, and university lecturer. Katarina has seen it all — and she’s here to share the real stories, the hard truths, and the clever strategies that can make or break your deal. In this episode, you’ll learn: ✔️ The biggest risks buyers face (and how to avoid stepping on legal landmines)✔️ What really happens during legal due diligence — and why it’s more than just paperwork✔️ How to deal with “deal fatigue” and who should keep cool when emotions run high✔️ Jaw-dropping stories of deals gone wrong — and the legal moves that could’ve saved them✔️ Clever deal structures and funding options that most people never think about✔️ How to avoid surprise legal bills (yes, it’s possible!)✔️ Why skipping legal help might be the most expensive mistake you ever make If you’ve ever felt overwhelmed by contracts, confused by due diligence, or just unsure about when to bring a lawyer in, this episode is your roadmap. 🎧 Tune in now and learn how to protect yourself, your deal, and your financial future — with smart legal strategy by your side.     Episode Highlights 02:50 – Why defining “online” vs “physical” businesses is crucial for strategy and contracts 07:10 – Ignoring a “change of control” clause led one buyer to lose supplier exclusivity overnight 08:15 – How proper due diligence helps uncover risks, negotiate price, and add protections 16:50 – Why non-compete agreements are critical to prevent the seller from becoming your competitor 21:40 – Managing emotions, trust, and “deal fatigue” is key to getting deals across the line 25:45 – Fixed legal fees and clear timelines reduce stress and prevent buyer fatigue 28:20 – Preparing buyers early for delays and emotional hurdles ensures smoother transactions   Key Takeaways ➥ Overlooking contract clauses (like change of control) can destroy business value overnight ➥ Buyers must normalize financials to reflect realistic salaries, working capital, and operational needs ➥ Strong non-compete agreements are non-negotiable to protect your investment ➥ Managing trust and emotions during diligence is just as important as the numbers ➥ Fixed-fee legal services and clear expectations help avoid surprises and fatigue ➥ Every deal involves risk — great advisors help you identify, price, and mitigate those risks effectively   About Katarina Strandberg Katarina Strandberg is a Swedish business lawyer specializing in venture capital, scale-ups, and M&A. She advises SME leaders and investors, drawing on her experience in deal structuring, fund law, and legislative work. A published author and angel investor, she’s also taught at Swedish universities and served on international advisory boards.   Connect with Katarina Strandberg ➥ https://www.youtube.com/@Businesslawtoolbox ➥https://www.stgcommerciallaw.com/    Resource Links ➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/ ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause ➥ Site Ground (Website Hosting) - https://bit.ly/3JBEC1u ➥ Link Whisper (SEO tool for internal linking on websites) - https://bit.ly/3l7K7Ld ➥ Active Campaign (Email Software Provider) - https://bit.ly/3DCwYQH   🔥Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO ➥ Investors Club - https://bit.ly/3ZpgioR     *This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.See omnystudio.com/listener for privacy information.

Strap in for a brutally honest conversation as Jaryd Krause sits down with none other than Elliot Holland,  a Harvard Business School alum, seasoned entrepreneur, and strategic founder. Elliot runs a seven-figure due diligence firm that performs "mini audits" on businesses, helping investors avoid being misled by clever sellers and slick brokers. With nearly 20 years of experience in small business acquisitions, Elliot has seen it all—and then some. From hidden red flags in financials to smoke-and-mirrors marketing metrics on Amazon and SEO-driven sites, he shares exactly where buyers get it wrong—and how those mistakes can cost you hundreds of thousands, or worse, your entire investment. This episode will pull back the curtain on how unsuspecting buyers get swindled into buying dud deals, all because they skipped real due diligence. Highlight the critical considerations buyers often miss in the acquisition process: ✔️ The most common (and costly) mistakes buyers make in due diligence✔️ Why relationships with sellers matter—and how they can go sideways fast✔️ How sellers can mislead or manipulate the narrative to close a deal✔️ Financial vs. marketing due diligence—what most acquirers overlook✔️ The frameworks Elliot uses to assess businesses like an expert This is not just theory—Elliot has personally helped countless clients dodge bad deals and secure multi-million-dollar wins, all by demystifying the due diligence process. With his signature humor, straight talk, and lived experience, he makes complex business buying principles not only clear but actionable. Whether you're a first-time acquirer or scaling your portfolio, this episode will save you more than money—it could save your sanity. Don’t even think about buying a business until you listen to this conversation.    Episode Highlights 04:15 – Red flags usually show as many small issues rather than one big problem 10:30 – Verifying seller’s time commitment by reviewing task lists and holding strategy meetings 18:45 – Wanting shortcuts in due diligence can lead to costly mistakes 23:00 – Sellers often resist reasonable buyer requests like strong non-competes and management interviews 26:10 – Negotiation is a strategic dance where sellers test buyer strength 29:15 – Cheaper advisors often bring higher risks and lower value on seven-figure deals   Key Takeaways ➥ Red flags are subtle and require a sharp, skeptical mindset to detect ➥ Sellers use stories and distractions instead of admitting flaws outright ➥ Due diligence takes time and can be uncomfortable but shortcuts are costly ➥ Experienced advisors are critical for high-value deals to avoid disaster ➥ Buyers need to be ready to walk away if sellers are not transparent or cooperative ➥ Emotional detachment helps buyers make better decisions and negotiate smarter   About Elliot Holland Elliott Holland is a Harvard Business School alum, former business acquirer & OG in small business acquisitions.  He runs TheBusinessBuyingMasterclass.com and a 7-figure business that does "mini audits" on businesses before clients acquire them to be sure they're not swindled.  With nearly two decades of experience, Elliott empowers everyday investors to acquire million-dollar businesses because he's been in their shoes and offers insight others cannot.   Elliott simplifies complex small business buying concepts with humor so that everyday investors can understand.   With over 100 podcast appearances and speaking engagements at top business schools, Elliott shares expertise on entrepreneurship, investing, and business buying.   Connect with Elliot Holland ➥ https://www.linkedin.com/in/elliottholland/   Resource Links ➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/ ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause ➥ Site Ground (Website Hosting) - https://bit.ly/3JBEC1u ➥ Link Whisper (SEO tool for internal linking on websites) - https://bit.ly/3l7K7Ld ➥ Active Campaign (Email Software Provider) - https://bit.ly/3DCwYQH 🔥Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO ➥ Investors Club - https://bit.ly/3ZpgioR   *This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.See omnystudio.com/listener for privacy information.

In this compelling episode, Jaryd Krause is joined by seasoned dealmaker and legal expert Jerome Fogel, partner at Fogel & Potamianos LLP, a boutique law firm specializing in high-stakes mergers, acquisitions, and capital raises. With a client list that spans venture funds, emerging tech companies, and elite athletes, Jerome offers a rare behind-the-scenes look at what it takes to structure smart, safe, and scalable business deals. Unpack the most critical questions aspiring buyers need to ask before acquiring an online business: ✔️ What are the hidden risks in buying or selling?✔️ How can poor team dynamics tank a deal?✔️ Should you use financing to buy a business—and what’s the best way to structure it?✔️ Where are the most promising online businesses being acquired today? Dive deep into the importance of due diligence, the common pitfalls buyers fall into, and how Jerome has helped high-profile clients—both on Wall Street and in the sports world—navigate complex transactions and build generational wealth. Whether you're looking to buy your first online business, scale your portfolio, or just want a masterclass in deal-making from someone who lives and breathes it, this episode delivers powerful insights and practical strategies. Don’t miss this one—it’s packed with value from start to finish.   Episode Highlights 04:45 – Current valuations explained, covering how tariffs and supply chain issues impact multiples and buyer decisions. 07:20 –  Typical ways buyers finance acquisitions, including credit lines, SBA loans, equity rollovers, and search funds. 10:55 – Major mistake buyers make by rushing post-acquisition integration without building trust within the team. 12:45 – What successful acquisitions have in common by retaining key team members and valuing the founder’s knowledge. 24:10 – Key risk prevention strategies involving thorough reps and warranties, clear earnout terms, strong IP protections, and precise legal language. 26:30 – Why clear definitions around risk and performance clauses are vital.   Key Takeaways ➥ M&A valuations currently range from 3–8x EBITDA for traditional companies and 10–15x for platform tech businesses, influenced heavily by tariffs and market uncertainty. ➥ Buyers typically operate in the $2M to $25M+ EBITDA range and rely on strong banking relationships, SBA loans, or creative financing like equity rollovers. ➥ Structuring deal terms clearly—especially reps and warranties and material adverse effect clauses—is critical to managing risk in acquisitions. ➥ Post-acquisition integration is one of the toughest challenges; involving existing teams and respecting founders’ knowledge leads to smoother transitions. ➥ Restrictive covenants are essential to prevent sellers from competing after the sale and protect buyer investments. ➥ Every deal is unique and requires customized, creative solutions; cookie-cutter approaches don’t work in M&A.   About Jerome Fogel Jerome Fogel is known as a dealmaker and innovator in the legal community. He is a partner with Fogel & Potamianos LLP and represents successful venture and hedge funds, corporations, and sports superstars.Fogel & Potamianos LLP is a boutique transactional firm that provides sophisticated counsel for buy-and-sell side mergers and acquisitions, fund formation, capital raises, and off-field sports transactions.Jerome has a 360-degree view of dealmaking, as he represents emerging companies raising capital, venture funds deploying capital, advisors and investors, and private companies in mergers and acquisitions.Jerome began his career in real estate finance at GE Capital. He is a graduate of the Haas School of Business (BS) and New York University School of Law (JD).   Connect with Jerome Fogel ➥ https://www.linkedin.com/in/jeromefogel/ ➥ www.fpgeneralcounsel.com   Resource Links ➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/ ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause ➥ Site Ground (Website Hosting) - https://bit.ly/3JBEC1u ➥ Link Whisper (SEO tool for internal linking on websites) - https://bit.ly/3l7K7Ld ➥ Active Campaign (Email Software Provider) - https://bit.ly/3DCwYQH   🔥Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO ➥ Investors Club - https://bit.ly/3ZpgioR   *This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.See omnystudio.com/listener for privacy information.

What if you could skip the struggle of starting a business from scratch—and step straight into profit? In this solo episode, Jaryd Krause pulls back the curtain on everything you need to know before buying your first (or next) profitable online business. No guest this time—just Jaryd, and over ten years of real-world experience helping thousands of people build financial freedom through smart acquisitions. This episode is a deep dive inspired by Jaryd’s most-watched YouTube content and the questions he hears constantly from aspiring buyers: Why should you buy a profitable business? How much should you invest? Should you use your cash or finance the deal? And where are people buying these businesses today? Get ready for a no-fluff breakdown of: ✔️ Why buying a profitable online business can fast-track your path to income and freedom✔️ How much capital do you need to get started (spoiler: it’s not always as much as you think)✔️ The truth about financing a deal—and what creative structures work✔️ Where to find legitimate, vetted businesses for sale right now✔️ The rookie mistakes that could cost you thousands—and how to avoid them This isn’t financial advice—but it is packed with insights from someone who’s helped people go from browsing listings to building six- and seven-figure digital business portfolios. If you’re ready to move from dreaming to doing, this episode will show you exactly what to consider, what to avoid, and where the real opportunities are in 2025’s online business marketplace. Hit play and take notes—this one’s loaded.   Episode Highlights 04:17 – Why buying a profitable online business is better than starting one from scratch? 07:38 – The ideal type of online business to acquire as a beginner. 13:24 – How much money should you invest when buying your first business? 18:43 – Why must you understand the ROI beyond just net profit? 27:46 – Myths around no-money-down deals and what real financing looks like. 31:22 – Where to find online businesses for sale: brokers vs. off-market deals?   Key Takeaways ➥ Buying an existing online business is less risky and faster than starting fresh, as you inherit proven systems, traffic, and revenue, reducing trial and error. ➥ “No money down” deals are rare and mostly involve distressed or declining businesses; most require some cash upfront. ➥ Acquisitions usually need a mix of cash, lender, and seller financing, with 10-20% cash upfront to show commitment. ➥ Reliable marketplaces like Empire Flippers, Quiet Light, and Flippa are great starting points for sourcing online businesses. ➥ Sellers often move on not because their business is failing but because of personal reasons like boredom or lifestyle changes, emphasizing the importance of proper due diligence before buying.   Connect with Jaryd Krause ➥https://www.linkedin.com/in/jarydkrause  ➥ $240K Income When Buying An Online Business - https://www.youtube.com/watch?v=G3yja-KnZzA&t=105s ➥Why Size Matters When Buying An Online Business - https://www.youtube.com/watch?v=7OWdl_n9rZI   Resource Links ➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/ ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause ➥ Hostinger (Website Hosting) - https://bit.ly/3HUqW0s ➥ SEM Rush (SEO tool) - https://bit.ly/3lINGaV ➥ Convert Kit (Email Software Provider) - https://bit.ly/3o10Xgx 🔥Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO ➥ Investors Club - https://bit.ly/3ZpgioR   *This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.See omnystudio.com/listener for privacy information.

Buckle up for an eye-opening episode where Jaryd Krause is joined by powerhouse entrepreneur and investor Justin Williams—a man who’s navigated everything from crippling six-figure debt to building and selling a multimillion-dollar business. Justin’s journey is far from ordinary. After dropping out of college, he and his wife, Tara, left their careers to pursue financial freedom. Their first business left them $120,000 in debt, living in a shared house with a newborn. Instead of quitting, they shifted to real estate, flipping over 100 houses a year and launching House Flipping HQ, a real estate education company that helped thousands succeed. Justin revealed how he sold his real estate education business for over $3.5 million—covering the why, when, and how. They dive into the unconventional yet strategic deal structure when selling to an operator already in the business. Then he delved into wealth building through business and real estate. Justin explains if he’d buy an online business, how he’d finance it, and the math behind buying a $2M business, hiring an operator, and earning $300K net profit annually without running it himself.   Gain insights on: ✔️ When is the right time to sell your business?✔️ The differences between investing in real estate vs. digital businesses✔️ How to build sustainable wealth without burning out✔️ And most powerfully—how Justin got through the lowest points of his journey. If you're looking for real talk about business, money, mindset, and freedom, this is the episode for you. Don’t miss this raw, high-energy conversation that’s packed with strategy, real numbers, and heart. Whether you're planning your first acquisition, prepping for a sale, or just needing motivation to keep pushing, this one will hit home.   Episode Highlights 03:00 – The journey to selling a $3.5M+ online business and lessons learned 08:20 – Using SBA loans to buy businesses vs. buying without them – pros, cons, and examples 10:50 – Buying businesses you don’t operate: how Justin makes it work and what to look for 17:35 – How Justin handled $120K in debt and overcame early financial struggles 23:40 – Managing expectations: The reality behind case studies and quick success stories 28:20 – Balancing ambition with lifestyle: Prioritizing family, health, and business growth 38:50 – Building habits and mentality for consistent progress versus just grinding Key Takeaways ➥ Everyone’s journey is different—don’t let case studies make you feel behind. ➥ Selling his $3.5M business was a strategic move to gain freedom and shift into a new season of life. ➥ A clean, simple business model and solid financials were critical in structuring a successful sale. ➥ SBA loans can be powerful tools for acquiring businesses, but creative financing is often just as effective. ➥ You don’t always have to operate the businesses you buy—systems, leadership, and delegation are key. ➥ Real estate offers stability while business offers higher returns—knowing when to lean into each is crucial. ➥ Long-term vision and emotional resilience helped Justin overcome $120K in debt and build real wealth.   About Justin Williams Justin Williams dropped out of college with a bold vision, convincing his wife, Tara, to leave her teaching job so they could start their first business. But their million-dollar dream quickly turned into a $120,000 debt nightmare. Determined to turn things around, they hustled out of debt and pivoted to real estate, eventually flipping 100 houses a year. Their success led them to launch House Flipping HQ, helping others build thriving real estate businesses. After selling the company, they took time off to focus on investments and new ventures.Now, as the founders of Millionaire University, their mission is simple: help people "graduate rich, NOT broke." With over 600,000 monthly podcast downloads, MU is transforming how entrepreneurs learn, grow businesses, and create wealth.     Connect with Justin Williams ➥ https://www.millionaireuniversity.com/    Resource Links ➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ ➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/ ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause ➥ Hostinger (Website Hosting) - https://bit.ly/3HUqW0s ➥ SEM Rush (SEO tool) - https://bit.ly/3lINGaV ➥ Convert Kit (Email Software Provider) - https://bit.ly/3o10Xgx  🔥Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO ➥ Investors Club - https://bit.ly/3ZpgioR   *This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.See omnystudio.com/listener for privacy information.

Get ready for a powerhouse episode as Jaryd Krause sits down with Andy Allaway, CEO of Empire Flippers—the leading platform for buying and selling online businesses. Andy brings nearly a decade of experience in the digital acquisition space, having both bought and sold businesses himself before joining Empire Flippers. With a background in scaling lean, remote-first teams and a passion for empowering global leadership, Andy shares his perspective on how the landscape of online business acquisitions has transformed over the years. Get a front-row seat to a conversation that spans from the early days of online business trading to today’s ever-evolving market. Andy and Jaryd explore how multiples have shifted, the role macroeconomic trends play in valuations, and what’s driving buyer and seller behavior in 2025. They unpack lessons from 2020’s acquisition boom, the downturn of 2023, and what savvy investors should prepare for in the years ahead. Deep dive into:✔️ How Empire Flippers has grown and adapted in a changing market✔️ Why multiples are where they are now—and what to expect next✔️ Financing six- and seven-figure deals (and what you need to know)✔️ The critical role of buyer-seller relationships in successful transactions✔️ New tariffs affecting e-commerce deals and how to navigate them✔️ The rise and fall of popular business models✔️ How AI is reshaping the acquisition game—for better and worse Plus, Andy offers actionable insights into which business models are thriving right now and shares real-world examples of where deals succeed or fall apart—and why. Whether you're preparing to buy, gearing up to sell, or simply want to understand how the digital business market is evolving, this conversation is a must-listen. Tune in to learn from one of the top minds in the space and gain clarity on where online business acquisitions are heading.   Episode Highlights 04:12 – What key metrics buyers look for when evaluating online businesses 10:05 – The importance of business simplicity and clean financials for buyers 13:20 – Different types of online business models currently in demand 16:45 – Strategies for improving business value before selling 23:50 – Challenges buyers face when scaling newly acquired online businesses 27:15 – The role of due diligence in successful business acquisitions 31:40 – Key trends shaping the future of buying and selling online businesses 35:05 – Advice for entrepreneurs considering acquisition as a growth strategy Key Takeaways ➥ Buyers prioritize clear, consistent financials and simplicity when evaluating online businesses to reduce risk and ensure scalability. ➥ Post-acquisition challenges often include scaling the business efficiently and managing growth without sacrificing quality. ➥ Market trends indicate increasing competition but also more opportunities for entrepreneurs leveraging online business acquisitions. ➥ Strategic acquisitions can accelerate growth for buyers, but understanding the nuances of each business model is essential. ➥ The exit process has evolved, with greater emphasis on protecting seller value through careful timing and market awareness.   About Andy Allaway   Andy Allaway is the CEO of Empire Flippers, the #1 place to buy and sell online businesses. With deep expertise in sales, operations, and leadership in remote settings, Andy builds lean, execution-driven remote companies that scale fast, deliver results, and give employees the freedom to live unconventional, high-impact lives. Passionate about empowering remote leaders, Andy is also the creator and host of "The Leader Sip," a YouTube channel dedicated to distilling practical insights from the best business and leadership books, tailored specifically for remote executives.   Connect with Andy Allaway ➥ https://bit.ly/3RtyMkE➥https://www.youtube.com/@theleadersip   Resource Links   ➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/ ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause ➥ Hostinger (Website Hosting) - https://bit.ly/3HUqW0s ➥ SEM Rush (SEO tool) - https://bit.ly/3lINGaV ➥ Convert Kit (Email Software Provider) - https://bit.ly/3o10Xgx   🔥Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥   ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO ➥ Investors Club - https://bit.ly/3ZpgioR   *This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.See omnystudio.com/listener for privacy information.